Reversal of Anomeric Selectivity with  O ‐Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis | Zendy

Kumar Amit | Zendy; Schmidt Richard R. | Zendy

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Reversal of Anomeric Selectivity with O ‐Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis

Author(s) -

Kumar Amit,

Schmidt Richard R.

Publication year - 2012

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201200138

Subject(s) - chemistry , glycosyl , trimethylsilyl trifluoromethanesulfonate , anomer , boron trifluoride , catalysis , trimethylsilyl cyanide , trifluoromethanesulfonate , glycosylation , trimethylsilyl , base (topology) , combinatorial chemistry , organic chemistry , selectivity , medicinal chemistry , stereochemistry , biochemistry , mathematical analysis , mathematics

Boron trifluoride or trimethylsilyl trifluoromethanesulfonate catalysed the generation of thioglycosides from O ‐glucopyranosyl or O ‐galactopyranosyl trichloroacetimidates and thiols giving mainly or exclusively α‐thioglycosides. However, the same reactions with phenylboron difluoride as catalyst are highly β‐selective. An S N 2‐type reaction course under acid/base catalysis is invoked by these and previous results.

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